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The concept of empathy is one that has become popular as a leadership ideal. We expect empathy from CEOs, ask designers to join empathy challenges, and tell people to put themselves in someone else’s shoes. Empathy is, at its simplest, knowing what someone else is going through. It’s often identified as a counterpart to sympathy and is seen as an important quality of modern leadership.

But setting empathy as a gold standard in leadership has its downfalls [1]. Empathetic leadership relies on personal experiences with situations that are atypical for you and assumes similar tolerance levels for discomfort. More importantly though, it assumes that experiencing something is the same as understanding.

Diversity doesn’t come without tension. The key is to know how to make it into jazz and not discordant noise.

Stereotypes are shortcuts our brains use to make fast decisions (especially when there is too much information or potential unknowns). We tend to infer a lot about others based on our past experiences, whether it’s accurate to do so or not. As the world becomes more connected and our interactions more immediate, we interact with people unlike us every day without even realizing it.

Our brains, being the prediction machines that they are, take these stereotypes and form an idea of how interactions will go.

Illustration: Design vs Development

As a quick example let’s look at the work-centric, cross-cultural environment between Design and Development.

A stereotypical concept of a Designer might be that they are:

untidy

unencumbered by deadlines

value form over function

generally “right-brained”

A stereotypical concept of a Developer might be that they are:

fastidious

unencumbered by manners

value function over form

generally “left-brained”

Objections over these questionable stereotypes aside, these two groups objectively look like completely different cultures. Each have their own language or jargon that sets them apart. The etiquette of how to interact with their work is different. Humor among these two groups can be impossibly nuanced, but it ties them together.

These things act as communication barriers and can hinder a process called the Negotiation of Meaning.

When I think back over the many communities I’ve been part of over the years — whether at work, as a volunteer, or in a church — those that were most vibrant had many things in common. They had leadership that was engaging, they had regular gatherings, and they were clear about who they served. As I’ve grown into my own concepts of leadership, I have come to recognize that one of the largest (and most hidden) things they had in common was a dedication to cultural safety. Letting people come as they are, and honoring that, was foundational to how they operated.

Safety can mean different things to different people, though, so here’s a quick overview of how I see it.

Types of Safety

Physical Safety – The ability to remain free from bodily harm. For my current work in the WordPress project, this mostly comes up in relation to in-person events.

Psychological Safety – The ability to express yourself freely. This comes up in all of the community’s communication channels, from Slack and team blogs to twitter and events.

Social Safety – The ability be your whole self among others. This, naturally, comes up in all of our spaces both in-person and on-line.

Moral Safety – The ability to reconcile your work with your morals. This comes up mostly with volunteers in WordPress.

Though I’m sure this isn’t a comprehensive list, I do feel that these four kinds of safety line right up with some basic needs of healthy modern communities: personal safety, open communication, inclusivity, and aligned values.

For no fewer than three years, my twitter bio has included the statement “I’m bad at writing recipes, great at cooking the food.” When I set out to define my leadership philosophy, I didn’t realize how true that statement would be.

I’ve been guiding and advising future leaders for many years, as a mentor and overall advocate, and my advice hasn’t changed much in that time. My concept of good leadership is informed by being a woman in a male-dominated field, a person of color in a primarily white-dominated world, and a general faith in the power of a good-hearted group of people.

As a high school student, I was regularly told to follow my passion. It’s the advice many teens are given specifically related to career aspirations, elective selection, and future college applications. Find what you’re passionate about and focus on that. It’s a trope that lines up beautifully with “love what you do and you’ll never work a day in your life”.

As I’ve progressed in my career, and taken on mentorship of those who will come after me, I’ve learned how perilous that advice can be.

Unknown Unknowns

When you receive the advice to follow your passion early in your life or your career, you have so many things you haven’t encountered yet. In my case, I was passionate about music. In part, I was passionate about it because I naturally excelled at music and I greatly disliked doing things I was bad at.

I focused intently on music with the ultimate end goal of “being famous*” since that’s what most musicians we know of are: famous. I didn’t realize that there were other parts of music that we going to be more appealing to me. Things like learning how to work in an ensemble, and how to guide an ensemble. Or the semantic language of music and its deep ties to math.

Passion Paradox

And while we’re on the subject of things we’re naturally good at, let’s talk about what makes you passionate. In order to enjoy a task, it’s important to have some level of mastery. So few people find joy in being bad at stuff (which is separate from enjoying new experiences). When we tell inexperienced people to follow their passions, we run the risk of cutting off the opportunity to grow their skills.

Consider lexicography.

This is one of those jobs that would make absolute sense for someone with a voracious love of reading, writing, and the ever-evolving nature of language. You might not suggest to any teen who loved reading that they “pursue professional reading” since there just aren’t that many job opportunities. Exposure to related work and fields is paramount to discovering those nuanced parts of what drives a passion.

Network Disadvantage

Not that this suggestion is perfect. I am aware that exposing your student to a broad spectrum of vocations isn’t possible for everyone. Take Your Child to Work Day gives them insight into your work world, which is of course helpful. Having a network that helps or encourages internships or job-shadowing is definitely a matter of privilege.

My best suggestion for broadening your knowledge without a network is to get a mentor. In my limited experience, it’s not been hard to get someone who is willing to mentor you. What is hard is being easy to mentor (and making the best use of everyone’s time).

Examined Pursuits

As with so many things, my recommendations boil down to “going in with your eyes open”. If you want to be famous, and you’ve learned all the many ways you can be in an industry without being the improbable star, yet still want to strive toward stardom then great. You have every right and you’re probably going to be amazing!

Just make sure that you take the time to know more about the entire landscape before you start.

* I have not, in case you missed it, gone on to be a famous musician. I work in technology.

From time to time I have the pleasure of introducing the concept of ex officio to groups I work with. It’s normally a concept reserved for non-profit boards, but I’ve found that its value goes far beyond that.

In the most basic terms, it refers to a position that participates in research, discussions, and overall analysis but has no voting power. In my experience, it’s held by former voting board members or close advisors.

“What’s this,” you say? “A board member who fights but never gets any power of voice?”

Not exactly.

As I said to my incomparable friend Helen today, I have infinite empathy, trust, and use for this type of voice in organizations.

The Strength to Move Forward

Good leaders know that one of their key responsibilities is to future-proof their organization. That means making sure you know who should take up the reigns after you, and who could take them up after that person. It means knowing that new ideas are how you stay relevant. It means knowing that having institutional knowledge isn’t the same as having visionary excellence.

There’s power in the ability to look the future of your cause (or company, or church) in the eye and say “I’ll help you remember what got us here, but it’s up to you to get us there.”

The Wisdom to Look Back

I’ve served in an ex officio capacity on a number of occasions. I bring over a decade of knowledge in non-profit service, leadership, and marketing to the table (among some other skills) and I have seen a lot of teams through growth and change. I am always delighted to offer that knowledge as a resource, without limits. A group mentor for learning leaders.

And that is the thing that always charms me most.

These learning leaders (regardless of their age) have asked you to do this so they can learn from the mistakes of others. Or so they can always have a concept of their roadmap by deciding where to go while also connecting to where they came from. Or so they don’t suffer through a solved problem.

Probably a little bit of each, if we’re honest.

The Space for Lasting Change

When you have a clear-eyed group of leaders and a selfless set of advisors, you can make more confident plans for future visions. You can forecast how a program will be received. You can gauge how long it takes your organization to embrace a new direction.

Most importantly, though, you set everything up for success and get to help train a new generation of powerful, life-changing voices.

Tips for the First-Time Ex Officio

Set aside the notion of “Only One Right Way” – Consider the possibility of “A Few Clearly Wrong Ways” and many ways that are basically right.

Present facts both positive and negative – A good resource tries to be balanced and this is no exception.

Don’t lobby – This isn’t the time to make carbon copies, it’s the time to uncover shared foundations. See item one.

Offer perspective proactively – There are so many unknowns. That’s why you’re there, to shine lights on mysterious spaces.

Refrain from “I told you so” – We all get it wrong sometimes. Shaming people forces inaction, not correction.

Practice tender discipline – Challenge people to do more than they are comfortable with, but work with what they have.

I’m a longtime organizer of local events, from happy hours to educational gatherings, and nothing makes me happier than seeing a crowd making connections and learning new things. As an unapologetic extrovert, I find every event I attend invigorating and joyful.

But I know that the world also has introverts and shy, but friendly people. For those people, things like Meetups are scary.

Meetups are great in theory. They gather people together based on nothing more than proximity and a shared interest with the sole intention of making friends out of strangers. It can be an ideal alternative for anyone who dislikes the advice “join a church” or “meet people at the gym”.

The hard part is making yourself attend these group events so you can meet people in real life.

Bring along a friend. They don’t have to use or know about WordPress. Friends for moral support are welcome at all events.

Don’t be too hard on yourself. You’ll hear, a lot, that WordPress is easy. I’m here to dispel that rumor – it’s the easiest of CMSs, all of which are hard. WordPress is the easiest difficult tool you’ll use to manage your content, so don’t worry when you get things wrong sometimes.

Ask specific questions if you’ve got them. Once you have become an expert in anything, it’s hard to know what non-experts need to know. If you’re new, bravely ask your questions even if you think they are dumb.

If WordPress is new to you, then take notes. You’ll need them later.

If WordPress isn’t new to you, then be prepared to hear new things. Flint sharpens flint.

Don’t let highly-skilled people scare you. WordPress was and always will be a brilliant blogging platform. Embrace it. Everyone started at zero. If you find a person who was born knowing WordPress, you let me know straight away!

Be brave enough to come back.

And I’d like to share my personal WP Meetup manifesto:

I will always greet you so you know you’re in the right place.

I will not condescend to you when I’m explaining things.

I will make room for vulnerability; admitting you don’t know something is hard.

I will make sure you’re invited to the table.

I will shed light, not heat.

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Where I’m Headed

Josepha is currently the Executive Director of the WordPress project, helping to coordinate and guide volunteer efforts across the ecosystem. Since 2015 she has worked behind the scenes as the lead of the open source division at Automattic. Her work includes financial planning, sponsorship relations, volunteer training programs, and several diversity initiatives on a global scale. She is well-versed in conflict mediation tactics and has a knack for explaining complex topics clearly and respectfully.